Synthesis of the first enantiomerically pure chiral bambusurils is reported. The bambusurils were prepared on the gram scale without using any chromatography techniques. The bambusurils formed supramolecular complexes with all tested chiral carboxylates including amino acids and drug molecules with the enantioselectivity ranging from 1.1 to 3.2.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/chem.201802748 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Reversing selectivity of bambusuril macrocycles toward inorganic anions by installing spacious substituents on their portals.
Chem Sci
January 2025
Department of Chemistry, Faculty of Science, Masaryk University Kamenice 5 625 00 Brno Czech Republic.
Two chiral bambusurils, which are diastereomers to each other, show remarkable differences in their binding affinity and selectivity toward inorganic anions as determined by isothermal titration calorimetry. These differences are explained by quantum-chemical calculations.
View Article and Find Full Text PDFBambusuril Macrocycles as Mediators of Supramolecular Interactions: Application to the Europium Cage Helicate.
Chemistry
March 2021
Department of Chemistry and RECETOX, Faculty of Science, Masaryk University, Kamenice 5, 62500, Brno, Czech Republic.
Herein, it is shown how bambusurils can be used for tuning and/or characterizing supramolecular systems. Indeed, the addition of bambusurils as anion scavengers to metal-mediated self-assemblies allows manipulation of the subtle equilibria in the given system. This is demonstrated for the case of the tetranuclear europium helical cage, which is well suited to different applications.
View Article and Find Full Text PDFFunctionalized Chiral Bambusurils: Synthesis and Host-Guest Interactions with Chiral Carboxylates.
Chempluschem
June 2020
Department of Chemistry and RECETOX Faculty of Science, Masaryk University, Kamenice 5, 625 00, Brno, Czech Republic.
Bambusurils are a class of macrocyclic anion receptors that exhibit notable anion recognition properties, able to bind various inorganic anions as well the carboxylates or sulfonates. Recently, we reported enantioselective recognition of chiral carboxylates using non-functionalized chiral bambusuril derivatives. Herein, we report the synthesis and host-guest properties of two new representatives of chiral bambusuril macrocycles bearing ester functional groups, differing by the substituents attached to their portals.
View Article and Find Full Text PDFInherently Chiral Bambus[4]urils.
J Org Chem
July 2020
Department of Natural Sciences, The Open University of Israel, Ra'anana 4353701, Israel.
A new class of bambus[4]urils (BU[4]s) composed of asymmetric ,'-disubstituted glycoluril subunits with different alkyl groups were designed, synthesized, and fully characterized by NMR techniques and X-ray crystallography. Structural studies showed that four macrocyclic diastereoisomers are possible: two symmetric achiral macrocycles and two macrocycles that are "inherently" chiral. The relative "head-to-tail" arrangement of the -substituents in BnMeBU[4], , clearly observed by X-ray spectroscopy analysis, determines the overall symmetry of the bambusuril structure.
View Article and Find Full Text PDFChiral Bambusurils for Enantioselective Recognition of Carboxylate Anion Guests.
Chemistry
October 2018
Department of Chemistry and RECETOX, Faculty of Science, Masaryk University, Kamenice 5, 625 00, Brno, Czech Republic.
Synthesis of the first enantiomerically pure chiral bambusurils is reported. The bambusurils were prepared on the gram scale without using any chromatography techniques. The bambusurils formed supramolecular complexes with all tested chiral carboxylates including amino acids and drug molecules with the enantioselectivity ranging from 1.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!